Tandem Protocol for Diversified Deuteration of Secondary Aliphatic Amines under Mild Conditions

Deuteration of amine compounds has been widely of concern because of its practical role in organic reaction mechanisms and drug research; however, only limited deuteration label methods are accessible with D2O as a deuterium source. Herein, we propose a convenient deuteration protocol, including preparing D2 by the AlGa activation method, using PtRu nanowires as catalysts, and utilizing the elementary step in the couple reaction involving an imine unit, to realize the rapid preparation of a secondary amine with a diversified deuteration label. The self-coupling between nitriles not only provides a symmetric secondary amine with four α-D atoms but also produces high-valued ND3 in an atomic-economic way.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-08-05
DOI
https://doi.org/10.1021/acs.joc.4c01089
Citations
5
Primary Topic
Chemical Reactions and Isotopes
Type
article
Field-Weighted Citation Impact
1.04

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article

Tandem Protocol for Diversified Deuteration of Secondary Aliphatic Amines under Mild Conditions

Ming‐Hao Du, Jian‐Ping Lang, Brendan F. Abrahams, Pierre Braunstein et al.
5 citations
The Journal of Organic Chemistry
Chemical Reactions and Isotopes
1.04
article

Tandem Protocol for Diversified Deuteration of Secondary Aliphatic Amines under Mild Conditions

Ming‐Hao Du, Jian‐Ping Lang, Brendan F. Abrahams, Pierre Braunstein, Hongwei Gu, Jianlin Yao, Bao-De Wu, Fengyuan Zhu
article en
5 citations

Abstract

Deuteration of amine compounds has been widely of concern because of its practical role in organic reaction mechanisms and drug research; however, only limited deuteration label methods are accessible with D2O as a deuterium source. Herein, we propose a convenient deuteration protocol, including preparing D2 by the AlGa activation method, using PtRu nanowires as catalysts, and utilizing the elementary step in the couple reaction involving an imine unit, to realize the rapid preparation of a secondary amine with a diversified deuteration label. The self-coupling between nitriles not only provides a symmetric secondary amine with four α-D atoms but also produces high-valued ND3 in an atomic-economic way.

The Journal of Organic ChemistryVol. 89(16)
Centre National de la Recherche Scientifique (FR), The University of Melbourne (AU), Chinese Academy of Sciences (CN), Soochow University (CN), Shanghai Institute of Organic Chemistry (CN), Institut de Chimie (FR), Université de Strasbourg (FR)
National Natural Science Foundation of China, Priority Academic Program Development of Jiangsu Higher Education Institutions, Collaborative Innovation Center of Suzhou Nano Science and Technology, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Science and Technology Program of Suzhou
Zero hunger
Openalex Percentile: Top 27%
Chemical Reactions and Isotopes
1.04
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Tandem Protocol for Diversified Deuteration of Secondary Aliphatic Amines under Mild Conditions — Ming‐Hao Du, Jian‐Ping Lang, et al. · The Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS